GB2464809A - Benzene derivatives useful for the treatment of ophthalmic diseases such as macular degeneration - Google Patents
Benzene derivatives useful for the treatment of ophthalmic diseases such as macular degeneration Download PDFInfo
- Publication number
- GB2464809A GB2464809A GB0918546A GB0918546A GB2464809A GB 2464809 A GB2464809 A GB 2464809A GB 0918546 A GB0918546 A GB 0918546A GB 0918546 A GB0918546 A GB 0918546A GB 2464809 A GB2464809 A GB 2464809A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- independently selected
- heterocyclyl
- carbocyclyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- 238000011282 treatment Methods 0.000 title description 8
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- 239000001257 hydrogen Substances 0.000 claims abstract description 691
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 567
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract description 380
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 338
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 325
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 33
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 98
- 125000005843 halogen group Chemical group 0.000 claims description 78
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 77
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- FPIPGXGPPPQFEQ-HPNHMNAASA-N 11-cis-retinol Natural products OCC=C(C)C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-HPNHMNAASA-N 0.000 claims description 39
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- WPWFMRDPTDEJJA-FAXVYDRBSA-N N-retinylidene-N-retinylethanolamine Chemical group C=1C(\C=C\C=C(/C)\C=C\C=2C(CCCC=2C)(C)C)=CC=[N+](CCO)C=1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C WPWFMRDPTDEJJA-FAXVYDRBSA-N 0.000 claims description 30
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
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- NCYCYZXNIZJOKI-IOUUIBBYSA-N 11-cis-retinal Chemical compound O=C/C=C(\C)/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-IOUUIBBYSA-N 0.000 claims description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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CN (1) | CN102197023B (ja) |
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Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2336117A1 (en) | 2005-05-26 | 2011-06-22 | Neuron Systems, Inc | Heterocyclic compounds for treating retinal diseases |
EA201100654A1 (ru) | 2008-10-22 | 2012-01-30 | Акусела, Инк. | Соединения для лечения офтальмологических заболеваний и расстройств |
IN2012DN00352A (ja) * | 2009-06-16 | 2015-08-21 | Bikam Pharmaceuticals Inc | |
CA2782015C (en) | 2009-12-11 | 2020-08-25 | Neuron Systems, Inc. | Topical ophthalmic compositions and methods for the treatment of macular degeneration |
US10463687B2 (en) | 2011-01-20 | 2019-11-05 | Cornell University | Treatments for retinal disorders |
EP2804605A4 (en) | 2012-01-20 | 2015-07-08 | Acucela Inc | SUBSTITUTED HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF DISEASES |
TW201406707A (zh) * | 2012-05-04 | 2014-02-16 | Acucela Inc | 用以治療糖尿病性視網膜病變及其他眼部疾病之方法 |
US9745291B2 (en) | 2012-12-21 | 2017-08-29 | Epizyme, Inc. | PRMT5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof |
DK2935222T3 (en) | 2012-12-21 | 2019-01-07 | Epizyme Inc | PRMT5 INHIBITORS AND APPLICATIONS THEREOF |
CA2899363A1 (en) | 2012-12-21 | 2014-06-26 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
WO2014100734A1 (en) | 2012-12-21 | 2014-06-26 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
JP2016505000A (ja) | 2012-12-21 | 2016-02-18 | エピザイム,インコーポレイティド | Prmt5阻害剤およびその使用 |
AU2014248878A1 (en) | 2013-03-12 | 2015-09-24 | Acucela Inc. | Substituted 3-phenylpropylamine derivatives for the treatment of ophthalmic diseases and disorders |
CN105934425B (zh) | 2013-11-15 | 2020-08-07 | 威斯塔解剖学和生物学研究所 | Ebna1抑制剂和其使用方法 |
EP3177288A4 (en) | 2014-08-04 | 2018-04-04 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
WO2016183534A1 (en) | 2015-05-14 | 2016-11-17 | The Wistar Institute Of Anatomy And Biology | Ebna1 inhibitors and methods using same |
EP4400106A1 (en) * | 2015-08-21 | 2024-07-17 | Aldeyra Therapeutics, Inc. | Deuterated compounds and uses thereof |
US11103159B2 (en) * | 2016-03-04 | 2021-08-31 | United States Of America As Represented By The Secretary Of The Air Force | Exhaled breath hypoxia biomarkers |
US11129823B2 (en) | 2016-05-09 | 2021-09-28 | Aldeyra Therapeutics, Inc. | Combination treatment of ocular inflammatory disorders and diseases |
US11040039B2 (en) | 2017-10-10 | 2021-06-22 | Aldeyra Therapeutics, Inc. | Treatment of inflammatory disorders |
CN112543634A (zh) | 2018-05-17 | 2021-03-23 | 威斯达研究所 | Ebna1抑制剂晶体形式及其制备和使用方法 |
EP3833660A4 (en) | 2018-08-06 | 2022-05-11 | Aldeyra Therapeutics, Inc. | POLYMORPHIC COMPOUNDS AND THEIR USES |
EP3856478A4 (en) | 2018-09-25 | 2022-06-08 | Aldeyra Therapeutics, Inc. | FORMULATIONS FOR THE TREATMENT OF DRY EYE DISEASE |
JP2022526917A (ja) | 2019-03-26 | 2022-05-27 | アルデイラ セラピューティクス, インコーポレイテッド | 眼科用製剤およびその使用 |
US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
JP2022530967A (ja) | 2019-05-02 | 2022-07-05 | アルデイラ セラピューティクス, インコーポレイテッド | 多形化合物およびその使用 |
JP2023526016A (ja) | 2020-05-13 | 2023-06-20 | アルデイラ セラピューティクス, インコーポレイテッド | 医薬製剤およびその使用 |
CN113191244A (zh) * | 2021-04-25 | 2021-07-30 | 上海夏数网络科技有限公司 | 一种驾驶员不规范行为检测方法 |
EP4351548A2 (en) | 2021-06-08 | 2024-04-17 | ATAI Therapeutics, Inc. | Dimethoxyphenylalkylamine activators of serotonin receptors |
KR20240019152A (ko) | 2021-06-09 | 2024-02-14 | 아타이 테라퓨틱스, 인크. | 신규 전구약물 및 디메틸트립타민의 접합체 |
US11827580B2 (en) | 2021-12-27 | 2023-11-28 | ATAI Life Sciences AG | Aminotetraline activators of serotonin receptors |
US12012381B2 (en) | 2021-12-30 | 2024-06-18 | Atai Therapeutics, Inc. | Dimethyltryptamine analogues as nitric oxide delivery drugs |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003059872A1 (en) * | 2001-12-31 | 2003-07-24 | Bayer Pharmaceuticals Corporation | Avb3 and avb5 integrin antagonists and methods of treating diseases or conditions associated with avb3 and avb5 integrins |
WO2006004795A2 (en) * | 2004-06-25 | 2006-01-12 | The Johns Hopkins University | Angiogenesis inhibitors |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2566271A (en) * | 1947-05-23 | 1951-08-28 | Eastman Kodak Co | Photographic developer containing substituted sulfonamide groups |
FR152F (ja) * | 1962-01-24 | |||
GB993584A (ja) * | 1962-01-24 | |||
US3236892A (en) * | 1963-03-25 | 1966-02-22 | Rexall Drug Chemical | Substituted phenylalkanolamines |
JPS4825932B1 (ja) * | 1969-08-28 | 1973-08-02 | ||
US3869442A (en) * | 1971-10-29 | 1975-03-04 | Eastman Kodak Co | Phenyl-azo-n-acylamidoethylaniline compounds |
DE2710997C3 (de) * | 1977-03-14 | 1980-08-14 | Dr. Karl Thomae Gmbh, 7950 Biberach | 4-Alkoxy carbonylamino-phenyläthanolamine, deren Herstellung und deren Verwendung als Arzneimittel |
US4252951A (en) * | 1979-10-09 | 1981-02-24 | Eli Lilly And Company | Isolation of syn-7-(2-amino-4-thiazolyl)-(methoxyimino)acetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid |
JPH0228112A (ja) * | 1988-04-21 | 1990-01-30 | Kaken Pharmaceut Co Ltd | 点眼用眼圧調整剤 |
KR100236806B1 (ko) | 1991-12-10 | 2000-01-15 | 시오노 요시히코 | 방향족 설폰아미드계 하이드록삼산 유도체 |
JP3421702B2 (ja) * | 1993-03-26 | 2003-06-30 | 大正製薬株式会社 | シグマ受容体拮抗薬 |
JP2759257B2 (ja) * | 1993-09-28 | 1998-05-28 | 大塚製薬株式会社 | 糖尿病治療剤 |
US5541228A (en) * | 1994-10-14 | 1996-07-30 | Bristol-Myers Squibb Co. | Melatonergic agents |
US5693804A (en) * | 1994-11-17 | 1997-12-02 | Molecular Geriatrics Corporation | Substituted 1-aryl-3-piperazin-1'-yl propanones |
KR100585348B1 (ko) * | 1997-10-08 | 2006-06-01 | 이소테크니카 인코포레이티드 | 중수소화된 시클로스포린 유사체 및 면역조절제로서 그의용도 |
US6331537B1 (en) | 1998-06-03 | 2001-12-18 | Gpi Nil Holdings, Inc. | Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds |
MXPA02006134A (es) * | 1999-12-21 | 2002-12-13 | Guilford Pharm Inc | Compuestos derivados de hidantoina, composiciones farmaceuticas y metodos de uso de los mismos. |
EP1248607A4 (en) * | 1999-12-21 | 2004-10-06 | Smithkline Beecham Corp | UROTENSIN II RECEPTOR ANTAGONISTS |
US20030134836A1 (en) * | 2001-01-12 | 2003-07-17 | Amgen Inc. | Substituted arylamine derivatives and methods of use |
US7102009B2 (en) * | 2001-01-12 | 2006-09-05 | Amgen Inc. | Substituted amine derivatives and methods of use |
US6878714B2 (en) * | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US20030032078A1 (en) * | 2001-01-23 | 2003-02-13 | Board Of Regents, The University Of Texas System | Methods and compositions for the treatment of macular and retinal degenerations |
JP2004535390A (ja) * | 2001-05-07 | 2004-11-25 | スミスクライン・ビーチャム・コーポレイション | スルホンアミド |
US6695888B2 (en) * | 2001-07-30 | 2004-02-24 | Unilever Home & Personal Care, Usa, Division Of Conopco, Inc. | Transition metal complexes as dye forming catalysts in hair coloring compositions |
PA8557501A1 (es) * | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
US6758866B2 (en) * | 2001-12-21 | 2004-07-06 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Enhanced color deposition for hair with sequestering agents |
US6737431B2 (en) * | 2002-03-12 | 2004-05-18 | Bristol-Myers Squibb Company | Benzoxazole derivatives as novel melatonergic agents |
US20030100580A1 (en) * | 2002-06-13 | 2003-05-29 | Dashyant Dhanak | Urotensin-II receptor antagonists |
US20040157836A1 (en) * | 2002-10-08 | 2004-08-12 | Comess Kenneth M. | Sulfonamides having antiangiogenic and anticancer activity |
CA2505397A1 (en) * | 2002-11-08 | 2004-05-21 | Warner-Lambert Company Llc | Phenylalkyl and pyridylalkyl piperazine derivatives |
CA2518655C (en) * | 2003-03-14 | 2015-06-09 | University Of Washington | Retinoid replacements and opsin agonists and methods for the use thereof |
WO2005054202A1 (en) * | 2003-11-25 | 2005-06-16 | Eli Lilly And Company | 7-phenyl-isoquinoline-5-sulfonylamino derivatives as inhibitors of akt (proteinkinase b) |
WO2005065050A2 (ja) | 2003-12-25 | 2005-07-21 | Asahi Kasei Pharma Corporation | 2環化合物 |
US7566808B2 (en) * | 2004-02-17 | 2009-07-28 | President And Fellows Of Harvard College | Management of ophthalmologic disorders, including macular degeneration |
US7786119B2 (en) * | 2004-04-01 | 2010-08-31 | Cardiome Pharma Corp. | Drug conjugates of ion channel modulating compounds |
EP1751136B1 (en) * | 2004-05-07 | 2014-07-02 | Amgen Inc. | Nitrogenated heterocyclic derivatives as protein kinase modulators and use for the treatment of angiogenesis and cancer |
MXPA06013022A (es) * | 2004-05-12 | 2007-01-23 | Squibb Bristol Myers Co | Antagonistas de urea de receptor p2y1 utiles en el tratamiento de condiciones tromboticas. |
US20060252107A1 (en) * | 2005-02-22 | 2006-11-09 | Acucela, Inc. | Compositions and methods for diagnosing and treating retinal diseases |
NZ563236A (en) * | 2005-05-13 | 2010-12-24 | Topotarget Uk Ltd | Pharmaceutical formulations of N-hydroxy-3-(3-phenylsulfamoyl-phenyl)-acrylamide, aka PXD-101, and arginine |
US20090182057A1 (en) * | 2006-05-26 | 2009-07-16 | Auspex Pharmaceuticals, Inc. | Deuterated aminoglycidal compounds |
BRPI0810063A2 (pt) | 2007-04-20 | 2014-10-14 | Acucela Inc | Composto, composição farmacêutica, e, métodos para modular fluxo de cromóforo em um ciclo retinóide, para tratar uma doença ou distúrbio oftálmico em um indivíduo, para inibir adaptação ao escuro em uma célula fotorreceptora de bastão da retina, para inibir regeneração de rodopsina em uma célula fotoreceptora de bastão da retina, para reduzir isquemia em um olho de um indivíduo, para inibir neovascularização na retina de um olho de um indivíduo, e para inibir degeneração de uma célula da retina em uma retina |
EA201100654A1 (ru) * | 2008-10-22 | 2012-01-30 | Акусела, Инк. | Соединения для лечения офтальмологических заболеваний и расстройств |
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2009
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- 2009-10-21 KR KR1020117011424A patent/KR101546562B1/ko not_active IP Right Cessation
- 2009-10-21 WO PCT/US2009/061545 patent/WO2010048332A2/en active Application Filing
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- 2009-10-21 EP EP09822658A patent/EP2340242A4/en not_active Withdrawn
- 2009-10-21 NZ NZ592993A patent/NZ592993A/xx not_active IP Right Cessation
- 2009-10-21 TW TW098135609A patent/TWI486326B/zh not_active IP Right Cessation
- 2009-10-21 AU AU2009308483A patent/AU2009308483C1/en not_active Ceased
- 2009-10-21 US US12/603,025 patent/US8674137B2/en not_active Expired - Fee Related
- 2009-10-21 BR BRPI0919920A patent/BRPI0919920A2/pt not_active IP Right Cessation
- 2009-10-21 CA CA2740952A patent/CA2740952C/en not_active Expired - Fee Related
- 2009-10-21 MX MX2011004315A patent/MX2011004315A/es active IP Right Grant
- 2009-10-22 GB GB0918546A patent/GB2464809A/en not_active Withdrawn
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2011
- 2011-04-12 CO CO11045312A patent/CO6361990A2/es not_active Application Discontinuation
- 2011-04-17 IL IL212404A patent/IL212404A0/en unknown
- 2011-04-21 CL CL2011000901A patent/CL2011000901A1/es unknown
- 2011-05-20 EC EC2011011067A patent/ECSP11011067A/es unknown
- 2011-11-23 HK HK11112714.7A patent/HK1158172A1/xx not_active IP Right Cessation
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2014
- 2014-02-07 US US14/175,959 patent/US9193669B2/en not_active Expired - Fee Related
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2015
- 2015-03-17 JP JP2015053695A patent/JP2015145392A/ja active Pending
- 2015-11-19 US US14/946,721 patent/US20160145198A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003059872A1 (en) * | 2001-12-31 | 2003-07-24 | Bayer Pharmaceuticals Corporation | Avb3 and avb5 integrin antagonists and methods of treating diseases or conditions associated with avb3 and avb5 integrins |
WO2006004795A2 (en) * | 2004-06-25 | 2006-01-12 | The Johns Hopkins University | Angiogenesis inhibitors |
Non-Patent Citations (5)
Title |
---|
CAPLUS Abstract Accession No. 2006:732343 & Journal of Medicinal Chemistry Vol. 49, No. 17, 2006, pages 5217-5225 * |
CHEMCATS Abstract Accession No. 2096242641 & UkrOrgSynthesis Building Blocks * |
CHEMCATS Abstract Accession No. 2096297761 & UkrOrgSynthesis Building Blocks * |
CHEMCATS Abstract Accession No. 2096597225 & UkrOrgSynthesis Building Blocks * |
CHEMCATS Abstract Accession No. 2096597704 & UkrOrgSynthesis Building Blocks * |
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